Long-range electron transfer (ET) in nature is believed to be affected by a bond mediated electron tunneling process known as a superexchange mechanism. Biological systems, however, are replete with chemical interactions other than covalent bonds, and these weaker chemical interactions may play a key role in facilitating biological ET. Since hydrogen bonding represents a major category of interaction type in biomolecular systems, we have studied electronic coupling pathways across hydrogen bonds. In particular, we have synthesized a model porphyrin system which consists of a electron donor and acceptor pair linked by a series of hydrogen bonds. Comparison of this system with a comparable system devoid of hydrogen bonding capabilities define how prominently hydrogen bonds mediate these ET events.